Herbicidal N-cyclohexadienyl heteroaryloxyacetamides

Abstract

The novel compounds of formula I: wherein Het represents an optionally substituted, optionally benzofused nitrogen containing 5- or 6-membered heteroaromatic group; R 1 represents an alkyl, alkoxyalkyl or cycloalkyl group; R 2 each independently represent an alkyl or alkenyl group, and m is 0 or an integer from 1 to 6, and herbicidal compositions containing such compounds as active ingredients can be utilized in various agricultural methods.

What is claimed is:  
     
       1. A compound of the general formula (I)                    
       wherein 
       Het represents an optionally substituted, optionally benzofused nitrogen containing 5- or 6-membered heteroaromatic group;  
       R 1  represents an alkyl, alkoxyalkyl or cycloalkyl group;  
       R 2  each independently represent an alkyl or alkenyl group, and  
       m represents 0 or an integer from 1 to 6.  
     
     
       2. A compound according to  claim 1  wherein R 2  each independently represent a C 1-4  alkyl or group C 2-4  alkenyl and m is 1, 2 or 3. 
     
     
       3. A compound according to  claim 1  wherein Het represents a thiadiazolyl, benzoxazolyl or benzothiazolyl group which may be substituted by one or more halogen atoms or alkyl, haloalkyl, haloalkoxy or phenyl groups. 
     
     
       4. A compound according to  claim 3  wherein Het represents a group selected from the formulae (1) and (2)                    
       in which 
       R 3  represents a hydrogen or halogen atom or an alkyl or haloalkyl group;  
       X represents O or S;  
       Y represents independently of each other a halogen atom or an optionally substituted alkyl group; and  
       n is an integer from 0 to 4.  
     
     
       5. A compound according to  claim 1  wherein R 2  represents a methyl group and m is 3. 
     
     
       6. A compound as claimed in  claim 1 , wherein R 1  represents a C 1-5  alkyl, a cyclopropyl or a 2-methoxyethyl group. 
     
     
       7. A compound of formula IA,                    
       wherein Het, R 1  and R 2  are as defined in  claim 1  and the dashed line indicates the presence of two conjugated double bonds in one or the other position with respect to the point of attachment of the nitrogen atom. 
     
     
       8. A compound according to  claim 7  selected from the formulae IA1 and IA2,                                      
       wherein 
       R 1  represents an alkyl or alkoxyalkyl group,  
       Het represents a group selected from the formulae (1) and (2)                    
        in which X has the meaning given, and  
       Y represents a halogen atom or a methyl group,  
       n is 0 or 1, and  
       R 3  represents a C 1-4  alkyl or C 1-4  fluoroalkyl group.  
     
     
       9. An isomeric mixture of the two compounds of formula IA of  claim 7  which differ only in the location of the conjugated double bonds. 
     
     
       10. The compounds according to  claim 1  selected from the group consisting of 
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-ethyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-ethyl-[1,3,4]-thiadiazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-ethyl-[1,3,4]-thiadiazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-ethyl-[1,3,4]-thiadiazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-ethyl-[1,3,4]-thiadiazol-2-yloxy)-N-ethyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-pentafluoroethyl-[1,3,4]-thiadiazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-pentafluoroethyl-[1,3,4]-thiadiazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-pentafluoroethyl-[1,3,4]-thiadiazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-pentafluoroethyl-[1,3,4]-thiadiazol-2-yloxy)-N-ethyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5- tert-butyl-[1,3,4]-thiadiazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5- tert-butyl-[1,3,4]-thiadiazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5- tert-butyl-[1,3,4]-thiadiazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5- tert-butyl-[1,3,4]-thiadiazol-2-yloxy)-N-ethyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-isopropyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-ethyl-[1,3,4]-thiadiazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-ethyl-[1,3,4]-thiadiazol-2-yloxy)-N-isopropyl-N-(3, 3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-pentafluoroethyl-[1,3,4]-thiadiazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-pentafluoroethyl-[1,3,4]-thiadiazol-2-yloxy)-N-isopropyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-tert-butyl-[1,3,4]-thiadiazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-tert-butyl-[1,3,4]-thiadiazol-2-yloxy)-N-isopropyl-N-(3,3,5-2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,5,5-trimethylcyclohexa-1, 3 -dienyl)-acetamide,  
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-cyclopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-trifluoromethyl-[1,3,4]-thiadiazol-2-yloxy)-N-cyclopropyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(benzoxazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(benzoxazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(benzoxazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(benzoxazol-2-yloxy)-N-ethyl- N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(benzoxazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(benzoxazol-2-yloxy)-N-isopropyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(benzoxazol -2-yloxy)-N-(2-methoxyethyl)-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(benzoxazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-chloro-benzoxazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-chloro-benzoxazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-chloro-benzoxazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-chloro-benzoxazol-2-yloxy)-N-ethyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-chloro-benzoxazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-chloro-benzoxazol-2-yloxy)-N-isopropyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(6-chloro-benzoxazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(6-chloro-benzoxazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(6-chloro-benzoxazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(6-chloro-benzoxazol-2-yloxy)-N-ethyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(benzoxazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(6-chloro-benzoxazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-chloro-benzoxazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-chloro-benzoxazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(6-chloro-benzoxazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(6-chloro-benzoxazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-methyl-benzoxazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-methyl-benzoxazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-methyl-benzoxazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-methyl-benzoxazol-2-yloxy)-N-ethyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-methyl-benzoxazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-methyl-benzoxazol-2-yloxy)-N-isopropyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(5-methyl-benzoxazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(5-methyl-benzoxazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(benzothiazol-2-yloxy)-N-methyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(benzothiazol-2-yloxy)-N-methyl-N-(3,3,5-trimethylcyclohexa-1,5-enyl)-acetamide,  
       2-(benzothiazol-2-yloxy)-N-ethyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(benzothiazol-2-yloxy)-N-ethyl-N-(3,3,5-trimethylcyclohexa-1,5-enyl)-acetamide,  
       2-(benzothiazol-2-yloxy)-N-isopropyl-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(benzothiazol-2-yloxy)-N-isopropyl-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide,  
       2-(benzothiazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,5,5-trimethylcyclohexa-1,3-dienyl)-acetamide,  
       2-(benzothiazol-2-yloxy)-N-(2-methoxyethyl)-N-(3,3,5-trimethylcyclohexa-1,5-dienyl)-acetamide.  
     
     
       11. A process for the preparation of a compound according to  claim 1  which comprises reacting a compound of the general formula II,                    
       in which R 1 , R 2  and m are defined in  claim 1  with a compound of general formula III, 
       
         
           Het—L 2   (III)  
         
       
       wherein Het represents an alkyl, alkoxyalkyl, or cycloalkyl group and one of L 1  and L 2  represents a hydroxy group and the other represents a leaving group. 
     
     
       12. A compound of the general formula II,                    
       in which R 1  represents an alkyl, alkoxyalkyl or cycloalkyl group; R 2  each independently represent an alkyl or alkenyl group, 
       m represents zero or an integer from 1 to 6, and  
       L 1  represents a hydroxy group or a leaving group selected from alkyl- and arylsulfonyl, alkyl- and arylsulfonyloxy, and perfluoroalkylsulfonyloxy groups.  
     
     
       13. A herbicidal composition comprising at least one compound according to  claim 1  and at least one agronomically acceptable carrier. 
     
     
       14. A composition according to  claim 13  comprising at least two carriers, at least one of which is a surface-active agent. 
     
     
       15. A method of combating undesired plant growth at a locus which comprises applying to the locus a herbicidally effective amount of a compound described in  claim 1 . 
     
     
       16. A method of combating undesired plant growth at a locus which comprises applying to the locus a herbicidally effective amount of a composition according to  claim 13 .